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Nano-aperture 30-element triphenylamine rigid macrocyclic compound and preparation method thereof

A technology of macrocyclic compounds and triphenylamine, which is applied in the direction of organic chemistry, can solve the problems of low conversion rate, can not be used as high carrier mobility material, etc., and achieve high total conversion rate, low cost and easy availability of raw materials Effect

Inactive Publication Date: 2010-06-23
NANJING UNIV OF INFORMATION SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage is: when synthesizing the precursor of linear hexamer, multi-step repeated coupling is required, and there are repeated group protection and deprotection. Therefore, even if the conversion rate of each step is high, the total conversion rate is still high. is very low
However, the disadvantage is that the precursors linked by covalent bond templates usually need to introduce specific functional groups at specific positions, and the connection of precursors to templates and the removal of templates after ring formation require additional reaction steps.
Patents US20090278442 and US20080248330 synthesized dendritic triphenylamine amorphous molecular glass structures, which are used in the design of organic light-emitting devices and storage devices respectively; patent CN101007904A reports the preparation of dye photosensitizers containing D-π-A triphenylamine structures for solar cells; and the patent CN101092403A thinks that such amorphous triphenylamine structures such as linear, star and dendritic structures cannot be used as high-carrier mobility materials, so a vinyl-linked triphenylamine with high mobility and high switching Ratio crystallizable cyclic triphenylamine as field effect transistor material

Method used

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  • Nano-aperture 30-element triphenylamine rigid macrocyclic compound and preparation method thereof
  • Nano-aperture 30-element triphenylamine rigid macrocyclic compound and preparation method thereof
  • Nano-aperture 30-element triphenylamine rigid macrocyclic compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Synthesis of 4-methyl-N-phenylaniline

[0047] In a 100mL single-necked flask, add 30mmol iodobenzene, 33mmol p-toluidine, 3mmol cuprous iodide, 6mmol L-proline, 60mmol K 2 CO 3 and 80 mL of DMSO. Under the protection of nitrogen, stir and heat to 110°C, keep the temperature for 24 hours; cool down to room temperature, add cold 2N hydrochloric acid to make the pH value reach 7, filter into a 250mL separatory funnel, extract three times with 50mL ethyl acetate each time, The organic phase was washed with saturated brine, then dried by adding anhydrous sodium sulfate, the solvent was removed under vacuum, and separated by column chromatography to obtain white floc 4-methyl-N-phenylaniline with a conversion rate of 45%.

[0048] The reaction equation is as follows:

[0049]

Embodiment 2

[0051] Synthesis of 4-bromo-N-phenyl-N-p-methylaniline

[0052] In a 100mL one-necked flask, add 18mmol p-bromoiodobenzene, 15mmol 4-methyl N-phenylaniline, 1.5mmol cuprous iodide, 3mmol L-proline, 30mmol K 2 CO 3 and 80 mL of DMSO. Under the protection of nitrogen, stir and heat to 110°C, keep the temperature for 24 hours; cool down to room temperature, add 2N hydrochloric acid to make the pH value reach 7, filter into a 250mL separatory funnel, extract three times with 25mL ethyl acetate each time, organic phase Wash with saturated brine, then add anhydrous sodium sulfate to dry; remove the solvent under vacuum, and separate through chromatography column to obtain white wax 4-bromo-N-phenyl-N-p-methylaniline, the conversion rate is 75%.

[0053] The reaction equation is as follows:

[0054]

Embodiment 3

[0056] Synthesis of 4-bromo-N-(4-bromophenyl)-N-phenylaniline

[0057] In a 100mL single-necked flask, add 30mmol aniline, 72mmol p-toluidine, 3mmol cuprous iodide, 6mmol L-proline, 60mmol K 2 CO 3 and 80mL of DMSO, under nitrogen protection, stirred, heated to 110°C, and kept at a constant temperature for 24 hours; lowered to room temperature, added 2N hydrochloric acid to make the pH value reach 7, filtered into a 250mL separatory funnel, each time with 50mL ethyl acetate Extracted three times, the organic phase was washed with saturated brine, and then dried by adding anhydrous sodium sulfate; the solvent was removed under vacuum; after separation by chromatography column, a white waxy substance, 4-bromo-N-(4-bromophenyl) -N-phenylaniline, the conversion rate was 88%.

[0058] The reaction equation is as follows:

[0059]

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Abstract

The invention belongs to the field of organic functional material, in particular to a nano-aperture 30-element triphenylamine rigid macrocyclic compound and a synthesis method thereof. The invention takes special functional group building triphenylamine and aliphatic ketone compound as raw materials and designs a construction unit which is provided with mutually reacting double functional groups (hydroxyl and active hydrogen) and is built at a certain angle; by Friedel-Crafts alkylate reaction, a ring is formed in one step under thermodynamic control so as to generate stable 30-element rigid triphenylamine electron-rich large ring under high conversion rate. By triphenylamine substation functional group variation, ketone structure variation or self-assembly functional group introduction, the macrocyclic compound can be widely applied to host material in host-guest chemistry to be self-assembled into hollow material by supermolecule and can serve as void guidance material and optical to electrical material with nano-aperture.

Description

technical field [0001] The invention belongs to the field of organic functional materials, and specifically relates to a kind of host material that can be widely used in photoelectric conversion materials and host-guest chemistry, and can be used as a hollow material through supramolecular self-assembly, and can also be used as a gap-conducting material with nanometer aperture. The triphenylamine nano-aperture rigid macrocycle compound, the invention also relates to the synthesis method of this compound. Background technique [0002] Inorganic nanoconductive, nanophotoconductive, and nanowaveguide materials have been extensively studied in recent years due to their diverse applications. Organic nanomaterials, especially organic small molecule nanomaterials, have strong designability in molecular structure, high luminous efficiency, and can implement orderly self-assembly through various means. Optical materials, and can be widely used in many aspects such as fluorescence de...

Claims

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Application Information

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IPC IPC(8): C07D255/04
Inventor 孔庆刚陈敏东郑有飞李俊周永慧郭照冰孔宁曹晓翠施健美
Owner NANJING UNIV OF INFORMATION SCI & TECH